Some assume the merits of risk to be self-evident (no A’s without F’s). Yet, this isn’t a commonly shared value among students, parents, or even peer educators; they often don’t understand risk and rarely advocate for it, seeking only “safe” opportunities. All students must embrace risk if they want to reach their potential and be prepared for the future that awaits. Let’s consider the benefits of risk-taking and how to manage and assess risk within experiential and outdoor learning environments. At Midland School in California, students chop their own kindling for fires, lead overnight horse-packing trips, and learn how to become responsible stewards of the land. They do all this while learning to be leaders amongst their peers, integrating 21st-century skills such as critical thinking and problem-solving in their endeavors. How can you help adolescents grow in their independence and leadership? Help them learn how to approach and manage risk in ways that build trust and collaboration alongside practical hands-on skills.